CN103864640A - N, N '-bis pyrene butyryl ornithine and application thereof - Google Patents
N, N '-bis pyrene butyryl ornithine and application thereof Download PDFInfo
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- CN103864640A CN103864640A CN201410069531.6A CN201410069531A CN103864640A CN 103864640 A CN103864640 A CN 103864640A CN 201410069531 A CN201410069531 A CN 201410069531A CN 103864640 A CN103864640 A CN 103864640A
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Abstract
The invention discloses a novel compound N, N '-bis pyrene butyryl ornithine and a preparation method and application thereof. The novel compound N, N '-bis pyrene butyryl ornithine is characterized in that the chemical formula is as shown in formula I shown in the specification; and the novel compound N, N '-bis pyrene butyryl ornithine can be used as a fluorescent ion probe of iron ion and lead ion and realizes the application of enriching the two ions. The invention also discloses a method for detecting the concentration of iron ion or lead ion based on an N, N '-bis pyrene butyryl ornithine probe. The invention also discloses a reversible recovery method for N, N '-bis pyrene butyryl ornithine serving as a lead ion probe. After reacting with the iron ion and lead ion, N, N '-bis pyrene butyryl ornithine produces precipitate, and thus the effect of enriching ions is realized; moreover, N, N '-bis pyrene butyryl ornithine does not react with any other metal ions, which proves the high specificity; in addition, N, N '-bis pyrene butyryl ornithine is easily prepared into aqueous solution, thus the convenience is provided for detecting the iron ion and lead ion; the operation is simple and convenient; the sensitivity is high; the recovery is easy; the environment is protected; and the practical application of the probe can be carried out easily.
Description
Technical field
The present invention relates to a kind of new compound nitrogen, nitrogen '-bis-pyrene butyryl radicals ornithine and application thereof.
Background technology
Lead is a kind of poisonous heavy metal element, and the damage that it can cause body multisystem, many organs, can cause a series of effects that are harmful to health such as encephalopathic, peripheral neuropathy, anaemia and renal failure.The intelligence of the lead of low dosage to children, grow and cause irreversible infringement.In this year, China's Lead contamination Health cost event takes place frequently, and " blood lead event " be current harm health of the masses, cause the heavy outstanding problem of heavy metal contamination of severe social influence.Equally, iron is being brought into play and important effect in life system, if take in the quantity not sufficient of iron or excessive, all can cause the disorder of physical function, thus cause anaemia, to liver and kidney cause damage, even cardiac failure of diabetes.But the detection method of lead ion and iron ion generally has atomic absorption spectrum and plasma emission spectroscopy, electrochemical method, colorimetry, biology and nano-sensor and fluorescent probe etc.But in these methods, there are some to need more sample or plant and instrument required also higher, being unsuitable in real time or in situ detection.And fluorescent probe has obtained everybody concern in advantages such as sensitivity, selectivity, validity, in situ detection.Be even more important so design and synthesize a kind of fluorescent ion probe that can detect plumbous and iron ion, and it is significant especially to remove the fluorescent ion probe of ion of ppm rank concentration.
Summary of the invention
One object of the present invention is to provide a kind of new compound, called after nitrogen, nitrogen '-bis-pyrene butyryl radicals ornithine.
Another object of the present invention is to provide nitrogen, nitrogen '-bis-pyrene butyryl radicals ornithine is as the application of iron ion and/or lead ion fluorescent ion probe.
Another object of the present invention be to provide a kind of based on nitrogen, nitrogen the iron ion of '-bis-pyrene butyryl radicals ornithine or the detection method of plumbum ion concentration.
The application of '-bis-pyrene butyryl radicals ornithine in enriched in iron ions and/or lead ion that another object of the present invention is to provide nitrogen, nitrogen.
Another object of the present invention is to provide the recovery method of a kind of above-mentioned nitrogen, nitrogen '-bis-pyrene butyryl radicals ornithine.
The technical solution used in the present invention is:
Nitrogen, nitrogen '-bis-pyrene butyryl radicals ornithine, its chemical formula is suc as formula shown in I:
（Ⅰ）。
A method that detects iron ion or plumbum ion concentration, comprises the steps:
1) production standard curve: in the ferric ion solutions of normal concentration or lead ion solution are joined to nitrogen claimed in claim 1, nitrogen '-bis-pyrene butyryl radicals ornithine solution, the change in fluorescence amount of '-bis-pyrene butyryl radicals ornithine solution that records ferric ion solutions or lead ion solution add-on and nitrogen, nitrogen, production standard curve;
2), in '-bis-pyrene butyryl radicals ornithine solution that again solution to be measured that contains iron ion or lead ion joined to nitrogen, nitrogen, record the change in fluorescence amount of this solution;
3) calculate the concentration of iron ion in solution to be measured or lead ion according to typical curve.
A kind of method that detects iron ion or plumbum ion concentration; in '-bis-pyrene butyryl radicals ornithine solution that comprises the nitrogen claimed in claim 1, the nitrogen that solution to be measured are joined to concentration known; until the fluorescence of nitrogen, nitrogen '-bis-pyrene butyryl radicals ornithine solution reaches maximum cancellation value; again according to the concentration of the add-on of liquid to be measured and nitrogen, nitrogen '-bis-pyrene butyryl radicals ornithine, calculate the concentration of iron ion in liquid to be measured or lead ion.
The application of nitrogen, nitrogen '-bis-pyrene butyryl radicals ornithine in enriched in iron ions and/or lead ion.
The application of nitrogen, nitrogen '-bis-pyrene butyryl radicals ornithine in enriched in iron ions and/or lead ion; operation steps is: by '-bis-pyrene butyryl radicals ornithine solution that drips nitrogen, nitrogen in the solution that contains iron ion and/or lead ion; be stirred to precipitation completely; to precipitate and solution separating; the title complex of be precipitated as nitrogen, nitrogen '-bis-pyrene butyryl radicals ornithine and iron ion and/or lead ion; be iron ion and/or the lead ion of enrichment, the solution of gained is the solution of having removed iron ion and/or lead ion.
The recovery method of nitrogen, nitrogen '-bis-pyrene butyryl radicals ornithine, comprises the following steps:
By nitrogen, nitrogen, the title complex of '-bis-pyrene butyryl radicals ornithine and lead ion adds the EDTA aqueous solution, stirs, and with organic solvent extraction, collects organic phase and organic solvent is removed in distillation, '-bis-pyrene butyryl radicals ornithine that obtains nitrogen, nitrogen.
Further, above-mentioned organic solvent is selected from least one in ethyl acetate, methylene dichloride, trichloromethane, benzene.
The invention has the beneficial effects as follows:
Nitrogen, nitrogen '-bis-pyrene butyryl radicals ornithine can be mixed with the aqueous solution easily, and can conveniently detect iron concentration or plumbum ion concentration, and susceptibility is high, operates also very convenient.
When with nitrogen, nitrogen, '-bis-pyrene butyryl radicals ornithine detects iron ion and/or iron ion; fluorescence shows very strong cancellation; and other common basic metal, alkaline-earth metal, heavy metal do not affect its detection, show the specificity that detects iron ion and/or lead ion.
Can there is coordination with iron ion and lead ion in nitrogen, nitrogen '-bis-pyrene butyryl radicals ornithine, produce precipitation in the aqueous solution, so just realized separating of iron ion and lead ion, reaches the effect of enrichment ion, reduces its harm to environment.
Nitrogen, nitrogen '-bis-pyrene butyryl radicals ornithine detects when lead ion, can utilize EDTA to reclaim, like this can this fluorescent ion probe of recycle, and environmental protection and energy saving, this is to nitrogen, nitrogen, and applying of '-bis-pyrene butyryl radicals ornithine has great importance.
Brief description of the drawings
Fig. 1 is that excitation wavelength is while being 350nm 2.0 × 10
-5in the nitrogen of mol/L, nitrogen '-bis-pyrene butyryl radicals ornithine solution, add the fluorescence spectrum figure of different amount iron ions;
Fig. 2 is 2.0 × 10
-5deposited phenomenon (a that the nitrogen of mol/L, nitrogen '-bis-pyrene butyryl radicals ornithine solution produces while adding the iron ion of equivalent, a left side is the solution of non-iron-ion, right is the solution containing iron ion) and fluorescence phenomenon (b under ultra violet lamp, a left side is the solution of non-iron-ion, and right is the solution containing iron ion);
Fig. 3 is that excitation wavelength is while being 350nm 2.0 × 10
-5in the nitrogen of mol/L, nitrogen '-bis-pyrene butyryl radicals ornithine solution, add the fluorescence spectrum figure of the lead ion of different concns;
Fig. 4 is 2.0 × 10
-5deposited phenomenon (a that the nitrogen of mol/L, nitrogen '-bis-pyrene butyryl radicals ornithine solution produces while adding the lead ion of equivalent, a left side is the solution without lead ion, right is the solution containing lead ion) and fluorescence phenomenon (b under ultra violet lamp, a left side is the solution without lead ion, and right is the solution containing lead ion);
Fig. 5 is 2.0 × 10
-5the nitrogen of mol/L, nitrogen '-bis-pyrene butyryl radicals ornithine solution adds the fluorescence spectrum variation diagram (excitation wavelength is 350nm) of various common metal;
Fig. 6 is 2.0 × 10
-5the nitrogen of mol/L, nitrogen '-bis-pyrene butyryl radicals ornithine solution precipitates with lead ion generation precipitation front and back and generation the fluorescence spectrum figure (excitation wavelength is 350nm) that adds EDTA afterwards; a curve is the fluorescence curve adding before lead ion; b adds lead ion to produce the fluorescence curve after precipitation, and c adds the fluorescence curve after EDTA after adding lead ion again.
Embodiment
In conjunction with the embodiments sub once the invention will be further described, but be not limited to this.
Synthesizing of nitrogen, nitrogen '-bis-pyrene butyryl radicals ornithine
The synthetic route of nitrogen, nitrogen '-bis-pyrene butyryl radicals ornithine is as follows:
Nitrogen, nitrogen '-bis-pyrene butyryl radicals ornithine structural formula is as shown in the formula I in synthetic route, and its concrete synthesis step is as follows:
1) by 0.10g(0.456mmol) ornithine methyl esters dihydrochloride add the methylene dichloride of 40.0mL, under the protection of nitrogen, add triethylamine (NEt3) and 0.27g (0.94mmol) the pyrene butyric acid of 1.26mL, and under bathing, cryosel stirs 5min, add again 0.38g(1.8mmol) DCC and 0.21g (1.8mmol) HOSU(N-N-Hydroxysuccinimide), continue again to stir 5min, then this mixed system is positioned over to continuation under room temperature and stirs 24h; By thin-layer chromatography detection reaction process, after question response, filter the solid of removing in solution, filtrate is washed 3 times with saturated sodium bicarbonate, be washed with water to again neutrality, organic phase anhydrous magnesium sulfate drying, suction filtration, revolve to steam and obtain crude product II(structural formula as shown in synthetic route except desolventizing), make developping agent by methylene dichloride and ethyl acetate and carry out silica gel column chromatography separating-purifying, obtain 152.2mg, productive rate is 48.6%.
2) getting 0.1g(0.146mmol) crude product II is dissolved in the NaOH solution of 40mL 1mol/L, stirring at room temperature 15h, after all dissolving, ethyl acetate washing 5 times for solution, to remove unreacted raw material and some by products, then water adds hydrochloric acid to slightly acidic (PH is about 5.5), has a large amount of white flosss to produce in solution, till by ethyl acetate, repeatedly extraction water solution to ethyl acetate layer does not have fluorescence again, now the product in the aqueous solution is extracted totally substantially; Collect ethyl acetate layer anhydrous magnesium sulfate drying, suction filtration, revolves to steam and removes solvent ethyl acetate; obtain thick product; make developping agent with ethyl acetate and methyl alcohol and carry out silica gel column chromatography separating-purifying, obtain Nitrogen in Products, nitrogen '-bis-pyrene butyryl radicals ornithine 74.6mg, productive rate is 76%.
Nitrogen, nitrogen '-bis-pyrene butyryl radicals ornithine structural formula as shown in the formula I in synthetic route, its
1h NMR composes (400MHz, DMSO-d
6) in chemical shift (ppm) and corresponding proton type affiliation be: 8.36-7.68 (m, 18
h, pyrenyl (
h )), 7.98 (t, 1
h,-CON
h cH
2-), 7.33-7.32 (d, 1
h,-CON
h cH-), 3.88 (m, 1
h,-C
h -), 3.27-3.23 (m, 4
h, PyC
h 2-), 3.03 (m, 2
h,-NHC
h 2-), 2.27-2.17 (m, 4
h,-NHCOC
h 2-), 1.96 (m, 4
h, PyCH
2c
h 2cH
2-), 1.57-1.44 (m, 4
h,-NHCH
2c
h 2cH
2the CHC of-+-
h 2cH
2-).
The mass spectrum result of nitrogen, nitrogen '-bis-pyrene butyryl radicals ornithine: ESI-MS (m/z): 671.8, theoretical molecular is 672.81.
embodiment 2
The detection method of iron ion or plumbum ion concentration
sensitivity detects:
Configuration concentration is 2.0 × 10
-5the nitrogen of mol/L, nitrogen '-bis-pyrene butyryl radicals ornithine solution, the strong solution of iron ion is dripped into, make the concentration of iron ion be respectively 0.0, 0.01, 0.05, 0.1, 0.25, 0.5, 1, 2, 5, 6, 8, 10, 12, 15, 18, 20, 22, 25, 28, 30, 33, 36, 40, 45, 50, 55, 60, 65, 70, 80, 90, 100, 120, 150 μ M, taking 350nm as excitation wavelength, record their fluorescence spectrum, fluorescence spectrum figure as shown in Figure 1, as we can see from the figure, along with the increase gradually of iron concentration, the intensity of fluorescence emission peak weakens gradually, and can see that adularescent floss precipitation separates out (as shown in the Fig. 2 of institute) gradually, Fig. 2 is 2.0 × 10
-5deposited phenomenon (a that the nitrogen of mol/L, nitrogen '-bis-pyrene butyryl radicals ornithine solution produces while adding the iron ion of equivalent, a left side is the solution of non-iron-ion, right is the solution containing iron ion) and fluorescence phenomenon (b under ultra violet lamp, a left side is the solution of non-iron-ion, right is the solution containing iron ion) fluorescence intensity of '-bis-pyrene butyryl radicals ornithine solution that as can be seen from the figure adds after lead ion nitrogen, nitrogen obviously weakens, in sum, nitrogen, nitrogen '-bis-pyrene butyryl radicals ornithine has gone out very high sensitivity to the detected representation of iron, and detectable minimum iron concentration reaches 0.01 μ M.
Equally, the strong solution of lead ion being added drop-wise to concentration is 2.0 × 10
-5in the nitrogen of mol/L, nitrogen '-bis-pyrene butyryl radicals ornithine solution, make the final concentration of lead ion be respectively 0.0,0.1,0.25; 0.5,1,2,3; 4,5,6,8; 10,12,15; 18,20,22; 25,28,30; 40,60,80; 100,120,150 μ M; taking 350nm as excitation wavelength, record the fluorescence spectrum figure (Fig. 3) of each concentration, also embody the increase gradually along with plumbum ion concentration; weakening gradually of fluorescence intensity, and be accompanied by separate out (as shown in Fig. 4 of institute) of the white floss precipitation that increases gradually, Fig. 4 is 2.0 × 10
-5deposited phenomenon (a that the nitrogen of mol/L, nitrogen '-bis-pyrene butyryl radicals ornithine solution produces while adding the lead ion of equivalent, a left side is the solution without lead ion, right is the solution containing lead ion) and fluorescence phenomenon (b under its ultra violet lamp, a left side is the solution without lead ion, right is the solution containing lead ion), the fluorescence intensity of '-bis-pyrene butyryl radicals ornithine solution that as can be seen from the figure adds after lead ion nitrogen, nitrogen obviously weakens; In sum, nitrogen, nitrogen '-bis-pyrene butyryl radicals ornithine also has very high sensitivity to plumbous detection, and detectable minimum plumbum ion concentration is 0.1 μ M.
specific detection:
Detect other metal by above-mentioned same step; comprise some heavy metals, basic metal, alkaline-earth metal and transition metal; these metals of result do not have the same phenomenon of generation and iron ion and lead ion; fluorescence intensity does not weaken; on nitrogen, nitrogen, the fluorescent emission character of '-bis-pyrene butyryl radicals ornithine does not almost affect, the changing value (I-I of nitrogen, nitrogen '-bis-pyrene butyryl radicals ornithine fluorescent emission peak-to-peak value when getting different concns metal ion and existing
0)/I
0mapping (Fig. 5) wherein I
0the intensity level of the fluorescence emission peak of '-bis-of nitrogen, nitrogen when representation metal ion concentration is 0.0 μ M pyrene butyryl radicals ornithine, the intensity level of the fluorescence emission peak of I represents nitrogen, nitrogen when the metal ion of different concns exists '-bis-pyrene butyryl radicals ornithine.
As shown in Figure 5, Hg
2+, Ca
2+, Co
2+fluorescent emission character Deng 14 heavy metal species ion pair nitrogen, nitrogen '-bis-pyrene butyryl radicals ornithine does not have a significant effect; '-bis-pyrene butyryl radicals ornithine that only has lead ion and iron ion can make nitrogen, nitrogen shows strong fluorescent quenching effect, nitrogen, nitrogen, and '-bis-pyrene butyryl radicals ornithine shows very high selectivity recognition reaction to lead ion and iron ion.
The detection of iron ion or plumbum ion concentration:
1) production standard curve: in the ferric ion solutions of normal concentration or lead ion solution are joined to nitrogen, nitrogen '-bis-pyrene butyryl radicals ornithine solution (experiment that working method detects with sensitivity), the change in fluorescence amount of '-bis-pyrene butyryl radicals ornithine solution that records ferric ion solutions or lead ion solution add-on and nitrogen, nitrogen, production standard curve;
2), in '-bis-pyrene butyryl radicals ornithine solution that again solution to be measured that contains iron ion or lead ion joined to nitrogen, nitrogen, record the change in fluorescence amount of this solution;
3) calculate the concentration of iron ion in solution to be measured or lead ion according to typical curve.
embodiment 3
The enriching method of nitrogen, nitrogen '-bis-pyrene butyryl radicals ornithine to iron ion and/or lead ion
By '-bis-pyrene butyryl radicals ornithine solution that drips nitrogen, nitrogen in the solution that contains iron ion and/or lead ion; stir; adularescent floss produces; Deng precipitation completely; centrifugal 10min under 10000r/min; obtain yellow solid (iron) and/or white solid (lead), and the liquid of gained is just for having removed the solution of iron ion and/or lead ion.
Above solid-liquid separation step, except can centrifugation technique, within the scope of those skilled in the art's understanding, can also adopt other method, as filtered.
embodiment 4
The recovery of nitrogen, nitrogen '-bis-pyrene butyryl radicals ornithine
Through Experimental Research constantly, find at nitrogen, after nitrogen '-bis-pyrene butyryl radicals ornithine and lead ion effect, add a certain amount of EDTA solution, nitrogen, the fluorescence intensity of nitrogen '-bis-pyrene butyryl radicals ornithine can be recovered significantly, as shown in Figure 6, in the time adding 100 times that the amount of substance of EDTA is lead ion, nitrogen, the fluorescence intensity of nitrogen '-bis-pyrene butyryl radicals ornithine returns to 87.89% of original state, this illustrates nitrogen, nitrogen '-bis-pyrene butyryl radicals ornithine is reversible for plumbous fluorescent ion probe, can efficient recovery nitrogen, nitrogen '-bis-pyrene butyryl radicals ornithine, more favourable practical application is provided.
The fluorescence spectrum of (a) in figure represents nitrogen, nitrogen '-bis-pyrene butyryl radicals ornithine solution; (b) in '-bis-pyrene butyryl radicals ornithine solution that represents nitrogen, nitrogen, add the fluorescence spectrum after lead ion, (c) representative adds 100 times of later fluorescence spectrums of (multiple of the amount of substance of lead ion) EDTA in (b) solution again.
The concrete operations of reclaiming:
The precipitation of get nitrogen, nitrogen '-bis-pyrene butyryl radicals ornithine and lead ion title complex; join in the EDTA aqueous solution; be uniformly mixed; utilize the ethyl acetate of 10 times of volumes to extract this aqueous solution; collect ethyl acetate layer distillation removal ethyl acetate; obtain solid, through mass spectroscopy, '-bis-pyrene butyryl radicals ornithine that proves to be nitrogen of the present invention, nitrogen.
In the present embodiment; nitrogen, nitrogen '-bis-pyrene butyryl radicals ornithine is 1: 100 with the precipitation of lead ion title complex and the amount of substance of EDTA ratio; certainly; in actually operating; the fluorescence intensity of the consumption of EDTA is to make nitrogen in solution, nitrogen '-bis-pyrene butyryl radicals ornithine returns to maximum value and is as the criterion; or appropriately adjust, all can realize to nitrogen, nitrogen the recovery of '-bis-pyrene butyryl radicals ornithine.In addition, except available ethyl acetate is as extraction agent, also can adopt other organic solvent, as methylene dichloride, trichloromethane, benzene etc. extract
Above embodiment is only for introducing preferred case of the present invention, and to those skilled in the art, any apparent changes and improvements of carrying out in the scope that does not deviate from spirit of the present invention, are all considered as a part of the present invention.
Claims (7)
1. nitrogen, nitrogen '-bis-pyrene butyryl radicals ornithine, its chemical formula is suc as formula shown in I:
2. a method that detects iron ion or plumbum ion concentration, is characterized in that: comprise the steps:
1) production standard curve: in the ferric ion solutions of normal concentration or lead ion solution are joined to nitrogen claimed in claim 1, nitrogen '-bis-pyrene butyryl radicals ornithine solution, the change in fluorescence amount of '-bis-pyrene butyryl radicals ornithine solution that records ferric ion solutions or lead ion solution add-on and nitrogen, nitrogen, production standard curve;
2), in '-bis-pyrene butyryl radicals ornithine solution that again solution to be measured that contains iron ion or lead ion joined to nitrogen, nitrogen, record the change in fluorescence amount of this solution;
3) calculate the concentration of iron ion in solution to be measured or lead ion according to typical curve.
3. one kind is detected the method for iron ion or plumbum ion concentration; in '-bis-pyrene butyryl radicals ornithine solution that comprises the nitrogen claimed in claim 1, the nitrogen that solution to be measured are joined to concentration known; until the fluorescence of nitrogen, nitrogen '-bis-pyrene butyryl radicals ornithine solution reaches maximum cancellation value; again according to the concentration of the add-on of liquid to be measured and nitrogen, nitrogen '-bis-pyrene butyryl radicals ornithine, calculate the concentration of iron ion in liquid to be measured or lead ion.
4. the application of nitrogen claimed in claim 1, nitrogen '-bis-pyrene butyryl radicals ornithine in enriched in iron ions and/or lead ion.
5. the application of nitrogen according to claim 4, nitrogen '-bis-pyrene butyryl radicals ornithine in enriched in iron ions and/or lead ion; it is characterized in that; its operation steps is: by '-bis-pyrene butyryl radicals ornithine solution that drips nitrogen, nitrogen in the solution that contains iron ion and/or lead ion; be stirred to precipitation completely; to precipitate and solution separating; the title complex of be precipitated as nitrogen, nitrogen '-bis-pyrene butyryl radicals ornithine and iron ion and/or lead ion; be iron ion and/or the lead ion of enrichment, the solution of gained is the solution of having removed iron ion and/or lead ion.
6. the recovery method of nitrogen claimed in claim 1, nitrogen '-bis-pyrene butyryl radicals ornithine; the title complex that it is characterized in that: comprise the following steps: by nitrogen, nitrogen '-bis-pyrene butyryl radicals ornithine and lead ion adds the EDTA aqueous solution; stir; with organic solvent extraction; collect organic phase and organic solvent, '-bis-pyrene butyryl radicals ornithine that obtains nitrogen, nitrogen are removed in distillation.
7. the recovery method of nitrogen according to claim 6, nitrogen '-bis-pyrene butyryl radicals ornithine, is characterized in that, described organic solvent is selected from least one in ethyl acetate, methylene dichloride, trichloromethane, benzene.
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| CN104402827A (en) * | 2014-10-23 | 2015-03-11 | 华南师范大学 | Preparation method and application of 2-(1-pyrenyl)-benzimidazole |
| CN105001852A (en) * | 2015-06-08 | 2015-10-28 | 济南大学 | Preparation method and application of magnetic pyrenebutyric acid fluorescent probe detecting ferric ions |
| CN114540012A (en) * | 2022-02-23 | 2022-05-27 | 华南师范大学 | Fluorescent molecular probe and application thereof in preparation of cancer cell detection reagent |
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| CN101153848A (en) * | 2007-10-10 | 2008-04-02 | 吉林大学 | Fluorescent ion probe and its application in ion detecting |
| CN102432492A (en) * | 2011-10-27 | 2012-05-02 | 华南师范大学 | N,N'-dipyrene butyryl lysine and application thereof |
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| CN101153848A (en) * | 2007-10-10 | 2008-04-02 | 吉林大学 | Fluorescent ion probe and its application in ion detecting |
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| HIDEYUKI YOSHIDA 等: "Liquid chromatographic determination of polyamines in human urine based on intramolecular excimer-forming fluorescence derivatization using 4-(1-pyrene)butanoyl chloride", 《BIOMEDICAL CHROMATOGRAPHY》, vol. 18, no. 9, 2 July 2004 (2004-07-02), pages 687 - 693 * |
| YOSHIDA, HIDEYUKI 等: "Liquid chromatographic determination of ornithine and lysine based on intramolecular excimer-forming fluorescence derivatization", 《ANALYTICAL SCIENCES》, vol. 17, no. 1, 31 January 2001 (2001-01-31), pages 108 - 1 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN104402827A (en) * | 2014-10-23 | 2015-03-11 | 华南师范大学 | Preparation method and application of 2-(1-pyrenyl)-benzimidazole |
| CN104402827B (en) * | 2014-10-23 | 2017-01-11 | 华南师范大学 | Preparation method and application of 2-(1-pyrenyl)-benzimidazole |
| CN105001852A (en) * | 2015-06-08 | 2015-10-28 | 济南大学 | Preparation method and application of magnetic pyrenebutyric acid fluorescent probe detecting ferric ions |
| CN114540012A (en) * | 2022-02-23 | 2022-05-27 | 华南师范大学 | Fluorescent molecular probe and application thereof in preparation of cancer cell detection reagent |
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